Cyanate Esters (i.e., Compounds Having The -ocn Group Bonded Directly To Carbon, Which Carbon May Be Single Bonded To Any Atom But May Be Multiple Bonded Only To Carbon) Patents (Class 560/301)
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Patent number: 10370569Abstract: A curable composition for bonding windings or core laminates in an electrical machine is presented. The curable composition includes: (A) about 10 weight percent to about 25 weight percent of a polyfunctional cyanate ester; (B) about 35 weight percent to about 65 weight percent of a first difunctional cyanate ester, or a prepolymer thereof; (C) about 15 weight percent to about 40 weight percent of a second difunctional cyanate ester, or a prepolymer thereof. An associated method is also presented.Type: GrantFiled: January 8, 2018Date of Patent: August 6, 2019Assignee: GENERAL ELECTRIC COMPANYInventors: Weijun Yin, Gary William Yeager, Kevin Warner Flanagan, David Andrew Simon, Eugene Pauling Boden, Kathryn Amanda Misner
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Patent number: 10338471Abstract: The composition for forming an underlayer film for lithography according to the present invention contains a compound represented by a specific formula (1) and 20 to 99% by mass of a solvent component (S), in which 27 to 100% by mass of the compound represented by the formula (1) is included in a component (A) other than the solvent component (S).Type: GrantFiled: July 31, 2015Date of Patent: July 2, 2019Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Kana Okada, Takashi Makinoshima, Masatoshi Echigo, Go Higashihara, Atsushi Okoshi
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Patent number: 8633328Abstract: Provided are saturated partially fluorinated alkoxy carboxylic acids or salts thereof and methods of preparation.Type: GrantFiled: April 15, 2013Date of Patent: January 21, 2014Assignee: 3M Innovative Properties CompanyInventors: Tilman C. Zipplies, Klaus Hintzer, Oleg Shyshkov
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Publication number: 20130281640Abstract: There is provided a novel dicyanatophenyl-based difunctional cyanate ester which is in a liquid form at ordinary temperature and can obtain a cured product having an excellent low thermal expansion rate. There is disclosed a cyanate ester compound represented by the following formula (I): (wherein R1 represents a hydrocarbon group having 2 to 20 carbon atoms).Type: ApplicationFiled: October 25, 2011Publication date: October 24, 2013Applicant: MITSUBISHI GAS CHEMICAL COMPANY, INC.Inventors: Makoto Tsubuku, Taketo Ikeno, Masayuki Katagiri, Tomoo Tsujimoto
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Publication number: 20130231494Abstract: Provided are saturated partially fluorinated alkoxy carboxylic acids or salts thereof and methods of preparation.Type: ApplicationFiled: April 15, 2013Publication date: September 5, 2013Applicant: 3M Innovative Properties CompanyInventors: Tilman C. Zipplies, Klaus Hintzer, Oleg Shyshkov
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Publication number: 20110118429Abstract: Charge transport materials are provided, and methods for making the same.Type: ApplicationFiled: December 23, 2005Publication date: May 19, 2011Applicant: E.I. DU PONT DE NEMOURS AND COMPANYInventors: Nora Sabrina Radu, Norman A. Herron, Gary Johansson
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Publication number: 20110009559Abstract: Aromatic dicyanate compounds which comprise aliphatic moieties having at least about six carbon atoms and resins and thermoset products based on these compounds.Type: ApplicationFiled: March 9, 2009Publication date: January 13, 2011Applicant: Dow Global Technologies Inc.Inventors: Michael J. Mullins, Robert E. Hefner, Ulrich Herold, Mark B. Wilson
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Patent number: 7674876Abstract: Novel hybrid monomers containing both the aryltrifluorovyinyloxyether-group (TFVE-group) and the cyanato-group, their synthesis, and the synthesis of polymers made from these new hybrid monomers are disclosed.Type: GrantFiled: May 24, 2006Date of Patent: March 9, 2010Assignees: Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V., Clemson UniversityInventors: Christian Dreyer, Monika Bauer, Suresh S. Iyer, Dennis W. Smith
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Patent number: 7202378Abstract: The present invention relates to a process for producing 5-nitro-3,4-dihydro-1(2H)-naphthalinone, 1,5-naphthalenediamine and 1,5-naphthalene diisocyanate, in which 4-(2-nitrophenyl)-n-butyronitrile is converted to 4-(2-nitrophenyl)-n-butyric acid.Type: GrantFiled: April 7, 2006Date of Patent: April 10, 2007Assignee: Bayer MaterialScience AGInventors: Joachim Zechlin, Kai Verkerk, Dietmar Wastian, Katrin Joschek, Tim Loddenkemper, Wilfried Pinke, Michael Schelhaas, Georg Ronge
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Patent number: 6800721Abstract: The unsaturated oligophenol cyanates of the general formula [A—]n[B—A—]xB[—A]m (I) in which A is a group of formula: and B is a group of formula: where R1, R2 and R3 are each hydrogen or a bond with a group B, there being either one or two bonds with group B; and both R4 and R4′ as well as R5 and R5′ separately or jointly represent a direct bond or hydrogen and a bond with a group A, there being either one or two bonds with A. The indices m and n are 0 or 1 but not both 1 at the same time and x is a whole number between 0 and 10, where at least one of the numbers, m, n and x is not 0. The unsaturated oligophenol cyanates can be prepared by reacting the corresponding oligophenols with cyanogen chloride. The have a low viscosity and owing to their double bonds are able to undergo free-radical polymerization.Type: GrantFiled: February 9, 2001Date of Patent: October 5, 2004Assignee: Lonza AGInventors: Ulrich Daum, Alessandro Falchetto
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Patent number: 6603035Abstract: Provided is a method for producing high purity cyanate derived from a phenol compound represented by the following formula (I): in the formula, each of A independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, X represents a single bond, an organic group having 1 to 20 carbon atoms, a carbonyl group, a sulfone group, a divalent sulfur atom or an oxygen atom, i and n represent an integer from 0 to 4. The cyanate contains low amount of impurities such as unreacted phenols and imidecarbonate, and is preferably used as a thermosetting resin for a sealing, laminate, composite material, molding material and adhesive for electric parts.Type: GrantFiled: August 20, 1999Date of Patent: August 5, 2003Assignee: Sumitomo Chemical Company, LimitedInventors: Satoshi Okamoto, Hisashi Watabu
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Patent number: 6458993Abstract: The present invention relates to novel aromatic cyanate ester compounds containing at least two rings linked by a group containing an unsaturated group. The present invention further relates to compositions and prepolymers of said novel aromatic cyanate ester compounds. The present invention further relates to a process for preparing said compounds and cured articles resulting from curable mixtures thereof.Type: GrantFiled: January 31, 2001Date of Patent: October 1, 2002Assignee: Vantico Inc.Inventors: Bor-Sheng Lin, Michael James Amone
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Patent number: 6380344Abstract: A cyanate ester-epoxy resin composition that can be cured to obtain a product which has excellent mechanical properties is provided. More particularly, a cyanate ester composition comprising (A) a cyanate ester in which the total content of impurities containing imino carbonates, alkyl cyanamides, partially substituted cyanates and phenols is 5% or less, or a prepolymer thereof and (B) an epoxy resin is provided.Type: GrantFiled: May 11, 1999Date of Patent: April 30, 2002Assignee: Sumitomo Chemical Company, Ltd.Inventors: Toshiaki Hayashi, Nobuyuki Nakajima
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Compositions containing cyanate ester and aromatic compounds having improved heat release properties
Patent number: 6365671Abstract: The present invention relates to compositions of matter containing aromatic cyanate ester containing at least two rings linked by a group containing an unsaturated group and selected aromatic hydroxyl compounds that exhibited improved heat release and curing properties. The present invention further relates to a process for preparing said compounds and cured articles resulting from curable mixtures thereof.Type: GrantFiled: June 26, 2000Date of Patent: April 2, 2002Assignee: Vantico Inc.Inventors: Bor-Sheng Lin, Michael James Amone -
Patent number: 6217943Abstract: A composition of matter comprises an aromatic cyanate ester silane comprising at least one cyanate ester group and at least one hydrolyzable silyl group. In the presence of a cyanate ester resin the aromatic cyanate ester silane acts as a coupling agent to improve the adhesion of the cyanate ester to a substrate. The curable compositions are useful as reinforced composites, and as adhesive and coating compositions.Type: GrantFiled: April 5, 1999Date of Patent: April 17, 2001Assignee: 3M Innovative Properties CompanyInventors: Joyce B. Hall, Fred B. McCormick, Kim M. Vogel, Hiroyaki Yamaguchi
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Patent number: 6150001Abstract: Reactive monomers of cyanate esters are vapor deposited onto thin film disks used for magnetic recording. The monomer films are then irradiated with ultraviolet (UV) light to polymerize the deposited monomer to form a solid, robust polycyanate ester overlayer on the disk that becomes smoother, more corrosion resistant and, when lubricated, more durable than disks without the overlayer. The polycyanate ester overlayer can either replace the conventional carbon overcoat or allow a substantially thinner carbon overcoat to be used.Type: GrantFiled: March 30, 1998Date of Patent: November 21, 2000Assignee: International Business Machines CorporationInventors: James Lupton Hedrick, Charles Mathew Mate, Junhua Wu
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Patent number: 6121484Abstract: Arylcyanates are produced by reacting polyvalent phenols with a halogen cyanogen in the presence of a tertiary amine and a nonaqueous solution at high temperature. The tertiary ammonium halogenide obtained as a secondary product is fully or partially removed by processing the reaction mixture with cationic and anionic exchanger, whereby arylcyanates with a particularly low halogenide content are obtained.Type: GrantFiled: May 21, 1999Date of Patent: September 19, 2000Assignee: Lonza AGInventor: Alessandro Falchetto
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Patent number: 5932762Abstract: A process for the production of aryl cyanates of the general formula I: ##STR1## A phenol of the general formula II: ##STR2## a tertiary amine and cyanogen chloride, of which at least one of the three components is present as a solution in an organic solvent, are fed essentially simultaneously and continuously at a temperature of -20.degree. C. to 0.degree. C. and in a molar ratio of cyanogen chloride to the reactive hydroxy groups of the phenol of 1.0:1.0 to 1.2:1.0 in a cooled loop reactor, so that the reaction components, before they come in contact with one another, are prediluted by the reaction mixture circulating in the loop reactor. Simultaneously, a stream of the reaction mixture corresponding to the fed volume of the reaction components is drawn off from the circulation.Type: GrantFiled: January 8, 1997Date of Patent: August 3, 1999Assignee: Lonza, Ltd.Inventors: Alessandro Falchetto, Ulrich Daum
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Patent number: 5912377Abstract: A composition of matter comprises an aromatic cyanate ester silane comprising at least one cyanate ester group and at least one hydrolyzable silyl group. In the presence of a cyanate ester resin the aromatic cyanate ester silane acts as a coupling agent to improve the adhesion of the cyanate ester to a substrate. The curable compositions are useful as reinforced composites, and as adhesive and coating compositions.Type: GrantFiled: June 5, 1996Date of Patent: June 15, 1999Assignee: Minnesota Mining and Manufacturing CompanyInventors: Joyce B. Hall, Kim M. Vogel, Fred B. McCormick, Hiroyaki Yamaguchi
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Patent number: 5866711Abstract: Fluorinated vinyl ethers having cyanate or carbamate groups are useful as monomers in making fluoropolymers having functional sites.Type: GrantFiled: July 23, 1997Date of Patent: February 2, 1999Assignee: E. I. du pont de Nemours and CompanyInventors: Ming-Hong Hung, Paul Douglas Brothers, Dewey Lynn Kerbow
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Patent number: 5648445Abstract: Allophanate-modified 1,3-phenylene diisocyanates or 1,1-biphenyl diisocyanates or 1,1'-oxy-bis-(isocyanato benzenes) which are storage stable liquid at 25.degree. C. are made by reacting the diisocyanate and a mono-alcohol to form an isocyanate containing urethane groups. The urethane groups in the diisocyanate are then converted to allophanate groups. The resultant product which has an isocyanate group content of from about 10 to about 40% may be further reacted with isocyanate-reactive compounds to produce an allophanate-modified diisocyanate prepolymer containing urethane or urea groups having an isocyanate group content of from about 5 to about 40.0%. The liquid, storage-stable, allophanate-modified diisocyanates produced by these processes are particularly useful in the production of elastomers and flexible foams.Type: GrantFiled: December 22, 1995Date of Patent: July 15, 1997Assignee: Bayer CorporationInventors: William E. Slack, Rick L. Adkins
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Patent number: 5563237Abstract: A cyanate resin composition suitable for a copper-clad laminate comprises components (A) and (B).(A) a cyanate compound of the formula: ##STR1## wherein R and Q each represents halogen, C.sub.1-10 alkyl, C.sub.5-7 cycloalkyl or C.sub.6-20 hydrocarbon; i and j each represents 0-4 and M is (2): ##STR2## wherein T represents halogen, C.sub.1-10 alkyl, C.sub.5-7 cycloalkyl or C.sub.6-20 hydrocarbon; k represents 0-10 and m represents 0-8, and(B) a hardener.Type: GrantFiled: February 23, 1994Date of Patent: October 8, 1996Assignee: Sumitomo Chemical Company, LimitedInventors: Yasuhiro Endo, Yoichi Ueda, Toshiaki Hayashi, Mitsuhiro Shibata, Shinichiro Kitayama, Shuichi Kanagawa, Hisashi Watabu
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Patent number: 5550282Abstract: Dislcosed is a curable composition of a partially trimerized prepolymer of the dicyanate ester of the formula ##STR1## wherein R.sub.1 and R.sub.2 are the same or different and each is alkyl, perfluoroalkyl, aryl or halogen; and A is a bridge selected from the group consisting of a direct bond, methylene optionally mono- or disubstituted by alkyl, perfluoroalkyl and/or aryl, a five or six membered cycloalkylene, sulfonyl, thio, oxy, carbonyl, phenylene, and xylylene optionally substituted by alkyl at on or both methylene carbon atoms is useful in the manufacture of electrical laminates having excellent dielectric properties in the GHz region.Type: GrantFiled: July 13, 1994Date of Patent: August 27, 1996Assignee: Kanegafuchi Kagaku Kogyo Kabushiki KaishaInventors: Hidenari Tsunemi, Toshinobu Nakata
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Patent number: 5488144Abstract: A novel dicyanate ester of the formula: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are the same or different and each is hydrogen, alkyl, perfluoroalkyl, aryl or halogen; A is a bridge selected from the group consisting of direct bond, methylene optionally mono- or di-substituted by alkyl, perfluoroalkyl and/or aryl, a five or six membered cycloalkylene, sulfonyl, thio, oxy, carbonyl, phenylene, and xylylene optionally substituted by alkyl at one or both methylene carbon atoms; with the proviso that when the cyanato group is at the para-position relative to the bridge A, both R.sub.1 and R.sub.2 are not hydrogen, and its prepolymer are useful in the manufacture of electrical laminates having excellent dielectric properties in GHz region.Type: GrantFiled: April 15, 1994Date of Patent: January 30, 1996Assignee: Kanegafuchi Kagaku Kogyo Kabushiki KaishaInventors: Hidenari Tsunemi, Toshinobu Nakata
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Patent number: 5420342Abstract: Bis(4-cyanatophenyl)-1,1-ethane, a low viscosity liquid, which is useful in wet filament winding, resin transfer molding and pultrusion processes is made by reacting cyanogen chloride dissolved in methylisobutylketone with a methylisobutylketone solution of bis(4-hydroxylphenyl)-1,1-ethane and a tertiary amine.Type: GrantFiled: November 19, 1993Date of Patent: May 30, 1995Assignee: Ciba-Geigy CorporationInventor: Wallace M. Craig, Jr.
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Patent number: 5374769Abstract: Novel polycyanate compositions containing one or more mesogenic moieties as lateral substituents are disclosed which provide improved processability relative to polycyanates containing one or more mesogenic moieties in the main chain of the molecule. Molecular level ordering of the resulting thermosets is maintained much similar to that found thermosets of polycyanates which have one or more mesogenic moieties in the main chain.Type: GrantFiled: December 24, 1992Date of Patent: December 20, 1994Assignee: The Dow Chemical CompanyInventors: Robert E. Hefner, Jr., Jimmy D. Earls
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Patent number: 5360887Abstract: A flame-retarded thermosetting resin composition is provided by blending about 5 to 45 mole % of a phenylcyanate having at least one halogen substituent at the ortho or para position relative to the cyanato group, and about 55 to 95 mole % of a halogen-free bis-4-phenylcyanate. A flame retardancy of V-O grade of UL94 is achieved in the thermoset resin of the composition without compromising dielectric, heat resistance, moisture absorption and other properties.Type: GrantFiled: July 28, 1993Date of Patent: November 1, 1994Assignee: Kanegafuchi Kagaku Kogyo Kabushiki KaishaInventors: Hidenari Tsunemi, Toshinobu Nakata, Koyoyuki Namura
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Patent number: 5340912Abstract: A cyanate-functional compound is provided which can be described by the formula ##STR1## in which Ar is a C.sub.6-20 aromatic moiety, L is a hexanenorbornane linking moiety, L' is a divalent cycloaliphatic moiety, and each of m and n is a number within the range of 0 to about 10. Such cyanate esters include the product of cyanation of the addition reaction of a phenol with a cyclohexene norbornene compound such as 5-(3-cyclohexen-1-yl)bicyclo[2.2.1]hept-2-ene. The resulting cyanate esters have low melt viscosity and low water absorbance in the cured state and are useful as the resinous component of high-performance electrical laminating and encapsulation formulations.Type: GrantFiled: February 23, 1993Date of Patent: August 23, 1994Assignee: Shell Oil CompanyInventors: Pen-Chung Wang, Donald R. Kelsey
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Patent number: 5292861Abstract: Trisphenol PA tricyanate, prepolymers and crosslinked polymers thereof are provided. Blends of trifunctional cyanates and fluorinated or non-fluorinated difunctional cyanate are provided. The crosslinked polymers exhibit low dielectric loss properties and high glass transition temperatures and are suitable as the matrix material for structural composites including printed circuit boards.Type: GrantFiled: December 29, 1992Date of Patent: March 8, 1994Assignee: International Business Machines CorporationInventor: Konstantinos I. Papathomas
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Patent number: 5284968Abstract: Bis(4-cyanatophenyl)-1,1-ethane, a low viscosity liquid, which is useful in wet filament winding, resin transfer molding and pultrusion processes is made by reacting cyanogen chloride dissolved in methylisobutylketone with a methylisobutylketone solution of bis(4-hydroxylphenyl)-1,1-ethane and a tertiary amine.Type: GrantFiled: September 30, 1991Date of Patent: February 8, 1994Assignee: Ciba-Geigy CorporationInventor: Wallace M. Craig, Jr.
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Patent number: 5162574Abstract: Bis(4-cyanatophenyl)-1,1-ethane, a low viscosity liquid, is useful in wet filament winding, resin transfer molding and pultrusion processes.Type: GrantFiled: September 13, 1990Date of Patent: November 10, 1992Assignee: Hi-Tek Polymers, Inc.Inventor: Wallace M. Craig, Jr.
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Patent number: 5149863Abstract: Cyanate esters of 4,4'-[1,3-phenylenebis(1-methylethylidene)] 2,2',6,6'-R-bisphenol when properly catalyzed, can be cured at temperatures in the range of about 250.degree. to about 300.degree. F. to obtain percent cyclotrimerization of the cyanate ester groups of at least 80 percent.Type: GrantFiled: August 12, 1991Date of Patent: September 22, 1992Assignee: Hi-Tek Polymers, Inc.Inventors: David A. Shimp, Jeffrey T. Vanderlip
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Patent number: 5142081Abstract: This present invention relates to a process for the preparation of O-silylated aliphatic hydroxyl, compounds by the reaction of aliphatic hydroxyl compounds with triorganochlorosilanes and removal of the resulting gaseous hydrogen chloride from the reaction mixture, characterized in that the reaction is carried out in the presence of phase transfer catalysts in the absence of solvent.The invention also relates to the use of the O-silylated hydroxyl compounds obtained by this process as starting materials for the preparation of isocyanates containing ester groups by a reaction with isocyanato carboxylic acid chlorides.Type: GrantFiled: October 10, 1990Date of Patent: August 25, 1992Assignee: Bayer AktiengesellschaftInventors: Lutz Schmalstieg, Josef Pedain, Klaus Nachtkamp
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Patent number: 5130454Abstract: Polytetrahydrofuran derivatives of the general formula ##STR1## where n is from 2 to 70, X is the bridge member --NH-- or --O-- and R.sup.1 and R.sup.4 are each hydrogen or various radicals.Type: GrantFiled: December 19, 1990Date of Patent: July 14, 1992Assignee: BASF AktiengesellschaftInventors: Eckhard Hickmann, Ulrich Koehler, Hardo Siegel
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Patent number: 5089660Abstract: A comonomer composition of an aromatic polycyanate and an aromatic monocyanate substituted at each position ortho to the cyanate group, and a polytriazine copolymer derived therefrom.Type: GrantFiled: January 22, 1988Date of Patent: February 18, 1992Assignee: The Dow Chemical CompanyInventors: Daniel J. Murray, Mitchell G. Dibbs, Philip C. Yang
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Patent number: 5068309Abstract: Cyanate esters of 4,4'-[1,3-phenylenebis (1-methylethylidene)] 2,2',6,6'-R-bisphenol when properly catalyzed, can be cured at temperatures in the range of about 250.degree. to about 300.degree. F. to obtain percent cyclotrimerization of the cyanate ester groups of at least 80 percent.Type: GrantFiled: March 29, 1990Date of Patent: November 26, 1991Assignee: Hi-Tek Polymers, Inc.Inventors: David A. Shimp, Jeffrey T. Vanderlip
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Patent number: 4983709Abstract: New aromatic compounds containing at least one cyanate ester and at least one propargyl ether group, each independently directly attached to a ring carbon atom(s), are useful in the preparation of resins having a low dielectric constant.Type: GrantFiled: December 2, 1988Date of Patent: January 8, 1991Assignee: Shell Oil CompanyInventor: Roy J. Jackson
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Patent number: 4981994Abstract: A base-catalyzed process is provided for the preparation of cyanate esters, the process including the step of pre-reacting a phenolic starting material with the basic catalyst and then reacting the pre-reaction product with a cyanogen halide. The process permits the preparation of cyanate esters in high yields at reaction temperatures above room temperature.Type: GrantFiled: July 31, 1989Date of Patent: January 1, 1991Assignee: Shell Oil CompanyInventor: Roy J. Jackson
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Patent number: 4944373Abstract: An asbestos-free disc brake pad is provided by employing a cyanate ester-based resin composition as binder. The disc brake pad exhibits consistent braking properties over a wide range of operating temperatures and an improved service life. Also the serious pollution problem due to use of asbestos in the conventional brake pads is removed.Type: GrantFiled: June 1, 1989Date of Patent: July 31, 1990Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Kazuyuki Ohya, Hidenori Kimbara
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Patent number: 4940848Abstract: Stable prepolymer solutions are made from partially cyclotrimerized 4,4'-thiodi(phenylcyanate) dissolved in cyclopentanone. The prepolymer solutions are used to make flame retardant and thermally stable laminates.Type: GrantFiled: November 10, 1988Date of Patent: July 10, 1990Assignee: Hi-Tek Polymers, Inc.Inventor: David A. Shimp
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Patent number: 4839442Abstract: Low viscosity dicyanate esters are made from bisphenols wherein the bridging member between the phenyl groups is unsymmetrical. These dicyanate esters are blended with prepolymers of dicyanate esters to form low viscosity non-crystallizing resins useful in preparing composites.Type: GrantFiled: June 20, 1988Date of Patent: June 13, 1989Assignee: Hi-Tek Polymers, Inc.Inventor: Wallace M. Craig, Jr.
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Patent number: 4820855Abstract: A process for producing a polyfunctional cyanate ester polymer which comprises heating at least one polyfunctional cyanate ester compound having the formula:R--OCN).sub.mwherein m is an integer of at least 2 and R is one or more aromatic organic groups, and the cyanato groups are bonded to the arylene ring, in the presence of a catalytic amount of a dialkyl tin oxide having the formula:R.sup.1 R.sup.2 SnOwherein each of R.sup.1 and R.sup.2 is C.sub.1 -C.sub.30 alkyl is disclosed.Type: GrantFiled: October 16, 1987Date of Patent: April 11, 1989Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Morio Gaku, Hidenori Kimbara
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Patent number: 4782178Abstract: Phenyl cyanates substituted at both ortho positions and further substituted with at least one halo at the meta or para positions are prepared. Then enhance ignition resistance, fire retardance, and toughness of polytriazines when added in varying amounts to polycyanate monomers before cure.Type: GrantFiled: November 13, 1987Date of Patent: November 1, 1988Assignee: The Dow Chemical CompanyInventors: James P. Godschalx, Daniel J. Murray, Abel Mendoza
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Patent number: 4752648Abstract: Chlorophosphines or thiophosphinic acid chlorides of the general formulae RPCl.sub.2, R.sub.2 PCl or R.sub.2 P(.dbd.S)Cl are made from feed materials selected from hydrogen-functional primary or secondary phosphines or secondary phosphine sulfides, where R stands for identical or different, linear or branched, substituted or unsubstituted alkyl radicals having from 1-16 carbon atoms, aryl radicals, aralkyl radicals or alkylaryl radicals having from 6-9 carbon atoms or cycloalkyl radicals having from 5-10 carbon atoms. To this end, the feed materials are reacted with phosphorus pentachloride, or with chlorine gas in the presence of phosphorus trichloride at temperatures within the range -78.degree. to +145.degree. C. It is possible for two radicals R to be linked together by one or two substituted or unsubstituted hydrocarbon chains having from 1-4 carbon atoms.Type: GrantFiled: September 18, 1986Date of Patent: June 21, 1988Inventors: Norbert Weferling, Werner Klose
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Patent number: 4751323Abstract: This invention relates to a polyaromatic cyanate which corresponds to the formula ##STR1## wherein Ar is an aromatic radical;B is a C.sub.7-20 polycyclic aliphatic radical;D is independently in each occurrence any non-active hydrogen-containing substituent;q, r and s are independently in each occurrence the integers b 0, 1, 2, l or b 3l ; with the proviso that the sum of q, 4 and s is greater than or equal to 2;t is independently in each occurrence an integer of between about 0 and 4 inclusive; andx is a number between about 0 and 5 inclusive.Another aspect of this invention is a novel polytriazine which comprises the reaction product of the polyaromatic cyanate esters of this invention. The novel polytriazines may further comprise the reaction product of the novel polyaromatic cyanates of this invention in admixture with other cyanates known in the art as useful for the preparation of polytriazines.Type: GrantFiled: November 16, 1983Date of Patent: June 14, 1988Assignee: The Dow Chemical CompanyInventors: Edmund P. Woo, Daniel J. Murray
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Patent number: 4748270Abstract: A process for the preparation of an aromatic cyanate which comprises (a) preparing in situ a cyanogen chloride by contacting a solution of chlorine in a chlorinated hydrocarbon with an aqueous solution of an alkali metal cyanide at a temperature of 0.degree. C. or below under conditions such that a cyanogen chloride is prepared; (b) physically separating the chlorinated hydrocarbon in which the cyanogen chloride is dissolved from the aqueous layer in which an alkali metal chloride salt is dissolved; and (c) contacting the cyanogen chloride dissolved in the chlorinated hydrocarbon with a hydroxy-substituted aromatic compound dissolved in a chlorinated hydrocarbon, a secondary alcohol or a tertiary alcohol, in the presence of a tertiary amine at a temperature of about 0.degree. C. or less under conditions such that a polyaromatic cyanate is prepared.Type: GrantFiled: November 16, 1983Date of Patent: May 31, 1988Assignee: The Dow Chemical CompanyInventors: Daniel J. Murray, Edmund P. Woo
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Patent number: 4745215Abstract: 4,4'-(Hexafluoroisopropylidene) bisphonol dicyanate and related compounds have reduced dielectric constant, reduced moisture absorption, and increase Tg making such compounds especially suitable for various electronic applications, such as circuit packaging or in forming prepregs and circuit boards.Type: GrantFiled: April 3, 1987Date of Patent: May 17, 1988Assignee: International Business Machines CorporationInventors: Robert J. Cox, William J. Summa, David W. Wang
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Patent number: 4647582Abstract: A compound of the formula: ##STR1## useful as a fungicidal agent against phytopathogenic fungi, and particularly against strains resistant to benzimidazole, thiophanate and/or cyclic imide fungicides.Type: GrantFiled: December 23, 1983Date of Patent: March 3, 1987Assignee: Sumitomo Chemical Company, LimitedInventors: Junya Takahashi, Toshiro Kato, Hiroshi Noguchi, Yukio Oguri, Shigeo Yamamoto, Katsuzo Kamoshita
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Patent number: 4612359Abstract: Thermosettable compositions are prepared which contain (A) from about 0.1 to 100 percent by weight of an esterified aromatic cyanate; (B) from zero to about 99.9 percent by weight of an aromatic polycyanate, an aromatic polycyanamide or mixture thereof and (C) from zero to about 99.9 percent by weight of an epoxy resin.Type: GrantFiled: October 16, 1985Date of Patent: September 16, 1986Assignee: The Dow Chemical CompanyInventor: Robert E. Hefner, Jr.